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The Rewards of Being Open to Chance: How a Serendipitous Hail Storm Changed My Career Path

Stephen Gillett
The Startup
Published in
4 min readNov 15, 2019

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The Rewards of Being Open to Chance: How a Serendipitous Hail Storm Changed My Career Path

The following is adapted from From Simi Valley to Silicon Valley.

Serendipity, the universe’s tendency toward happy accidents, is no joke. In fact, I credit much of my overall career path to the fact that I stayed open to unanticipated detours, and I believe there’s value in you doing the same.

You can try to map out every minute detail of your life, which might get you from Point A to Point B. But, in the process of sticking to a rigidly structured map, you may very well miss out on detours you don’t even know exist, like life-changing career opportunities or influential new relationships.

If you’re not convinced there’s anything to be gained by chance, let’s take a look at how serendipity shaped my career — and what it means for you to stay open to it.

A Hail Storm of Opportunity

In the early 2000s, as I was in the process of looking into potential openings at Seattle-based companies like Amazon and Microsoft, I got a call from a company I had never heard of called Corbis. The woman on the other end of the line told me her name was Sue McDonald, and that she was the CFO of the company. “We’re looking for a head of technology,” she told me.

It turned out that this company I had never heard of was owned by Bill Gates. In 1989, Gates had begun traveling around the world, purchasing the rights to black and white photos of things like the Eiffel Tower, the Great Wall of China, and Muhammad Ali. Corbis then sold the rights to use these photos, like the black and white version of Getty images.

After hearing what Sue had to say, I decided I was still more interested in joining a company like Microsoft or Amazon, so I politely declined. We hung up and I didn’t think about the conversation beyond that.

A few days later, security called from the front desk at Yahoo!, where I was working at the time. “Sue McDonald is here to see you,” they said.

Why would she be here? I wondered. “I don’t have an appointment,” I told security.

“Well,” they replied, “she’s here and she’s insisting that you guys meet.”

I went down to the lobby and found Sue waiting for me. “Do you have some time?” she asked.

At that very moment, the weather changed quickly; it began to hail like something out of a sci-fi movie, which isn’t exactly the norm in Sunnyvale, California. I turned to Sue and said, “Well, if there’s any sort of divine message that we should meet, this is it.”

We stood there for a few moments, looking out the window and watching the hail crash down to the ground before I led her into the cafeteria to chat.

By the end of this unplanned conversation, I was intrigued. I agreed to fly up to Seattle to interview and boom! Next thing I knew, I had the job — my first senior vice president job (which later became my first CIO position).

Serendipity Is Real — and You Can Seize It

Because of my recruitment to Corbis and so many other events in my life, I’ve learned that serendipity is about much more than just being in the right place at the right time. Far more importantly, it requires a flexible, open mindset and a willingness to take some risk. It is only with this that we can allow unexpected people and circumstances to come into our life and transform it.

As an avid lifelong gamer, I think of serendipitous detours as side quests. Often, it is along these side quests, where we find opportunities to challenge ourselves, that the most profound and unexpected joy and growth await. These challenges might include everything from meeting someone special to signing up for a new role at work.

Most of the important things in life require a certain amount of effort on your part, but they also involve an undeniable element of alchemy. If you stay open to new possibilities and let serendipity do its work, you maximize your chances of finding your most fulfilling career path.

You know what they say: when you hear opportunity knock, it’s up to you to open the door and let it in.

For more advice on forging your career path, you can find From Simi Valley to Silicon Valley on Amazon.

Stephen Gillett is the co-founder and CEO at Chronicle — an Alphabet company born out of X, The Moonshot Factory — and is an executive advisor to the CEO at Google. As one of the youngest CIOs of a Fortune 500 company in history, he was responsible for leading the technological transformation of Starbucks under Howard Schultz. Stephen’s previous positions included CIO at Corbis, working directly with Bill Gates; President at Best Buy; and COO at Symantec. As an avid lifelong gamer, Wired also recognized him as an innovative Guild Master in World of Warcraft. Stephen lives in Silicon Valley with his high school sweetheart and their eight children. Stephen can be reached at SVtoSV@gillett.org.

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Stephen Gillett
The Startup

Father and Gamer. Founder, Entrepreneur, Operator and Amazon Best Selling Author. Executive Advisor. Investor. Go Ducks! جلاد